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Preparation process of 2-iodo-3-bromo-5-chloropyridine

A technology of chloropyridine and elemental iodine, applied in the field of preparation of 2-iodo-3-bromo-5-chloropyridine, can solve the problems of harsh reaction conditions, many by-products, troublesome post-processing operations, etc., and achieves mild reaction conditions, Environmentally friendly, cheap and easy-to-obtain raw materials

Inactive Publication Date: 2017-03-01
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction conditions in the process route are harsh, and the reaction must be carried out at -75°C; there are many by-products, which must be purified by basic alumina column chromatography, recrystallization, etc., and the post-treatment operation is troublesome

Method used

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  • Preparation process of 2-iodo-3-bromo-5-chloropyridine
  • Preparation process of 2-iodo-3-bromo-5-chloropyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Under nitrogen protection, acetonitrile (100mL), elemental iodine (44.0g, 173.5mmol), cuprous iodide (18.4g, 96.4mmol) and tert-butyl nitrite (13.9g, 135.0mmol) were successively added into a 500mL three-necked flask , and then slowly added 2-amino-3-bromo-5-chloropyridine (20.0 g, 96.4 mmol) under ice bath, and reacted at 60° C. for 2 h. After completion of the reaction, add water (45mL), filter with suction, rinse the filter cake with ethyl acetate (45mL×1), extract the filtrate with ethyl acetate (200mL×2), combine the organic phases, and wash with saturated aqueous sodium thiosulfate ( 100mL×2), washed with anhydrous sodium sulfate, evaporated to remove the solvent under reduced pressure, the residue was slurried with a small amount of methanol, filtered with suction, and the filter cake was dried to obtain 21.5g of 2-iodo-3-bromo-5-chloropyridine as a white solid , the yield was 70.0%.

[0013] 1 H-NMR (CDCl 3 , 400MHz,), δ: 7.835(d,1H), 8.304(d,1H); MS, m / z: 32...

Embodiment 2

[0015] Under nitrogen protection, acetonitrile (100mL), elemental iodine (48.9g, 192.8mmol), cuprous iodide (18.4g, 96.4mmol) and tert-butyl nitrite (14.9g, 144.6mmol) were successively added into a 500mL three-necked flask , and then slowly added 2-amino-3-bromo-5-chloropyridine (20.0 g, 96.4 mmol) under ice bath, and reacted at 60° C. for 2 h. After completion of the reaction, add water (45mL), filter with suction, rinse the filter cake with ethyl acetate (45mL×1), extract the filtrate with ethyl acetate (200mL×2), combine the organic phases, and wash with saturated aqueous sodium thiosulfate ( 110mL×2), washed with anhydrous sodium sulfate, evaporated to remove the solvent under reduced pressure, the residue was slurried with a small amount of methanol, filtered with suction, and the filter cake was dried to obtain 21.4g of 2-iodo-3-bromo-5-chloropyridine as a white solid , the yield was 69.6%.

[0016] 1 H-NMR (CDCl 3， 400MHz,), δ: 7.835(d,1H), 8.304(d,1H); MS, m / z: 323...

Embodiment 3

[0018] Under nitrogen protection, acetonitrile (100mL), elemental iodine (53.8g, 212.1mmol), cuprous iodide (20.2g, 106.0mmol) and tert-butyl nitrite (13.9g, 135.0mmol) were successively added into a 500mL three-necked flask , and then slowly added 2-amino-3-bromo-5-chloropyridine (20.0 g, 96.4 mmol) under ice bath, and reacted at 60° C. for 2 h. After completion of the reaction, add water (45mL), filter with suction, rinse the filter cake with ethyl acetate (45mL×1), extract the filtrate with ethyl acetate (200mL×2), combine the organic phases, and wash with saturated aqueous sodium thiosulfate ( 110mL×2), washed with anhydrous sodium sulfate, evaporated to remove the solvent under reduced pressure, the residue was slurried with a small amount of methanol, filtered with suction, and the filter cake was dried to obtain 21.6g of 2-iodo-3-bromo-5-chloropyridine as a white solid , and the yield was 70.3%.

[0019] 1 H-NMR (CDCl 3， 400MHz,), δ: 7.835(d,1H), 8.304(d,1H); MS, m / z...

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Abstract

The invention discloses a preparation process of 2-iodo-3-bromo-5-chloropyridine, wherein with 2-amino-3-bromo-5-chloropyridine is employed as a raw material and is subjected to a one-step reaction to synthesize the target product 2-iodo-3-bromo-5-chloropyridine, total yield reaching 71.2%. The preparation process employs low-cost and easy-to-obtained raw materials, has mild and easy-to-control reaction conditions, simple and convenient after treatment and high yield, and is easy to industrially apply.

Description

technical field [0001] The invention relates to a preparation process of 2-iodo-3-bromo-5-chloropyridine. Background technique [0002] In recent years, the research on pyridine and its derivatives has attracted more and more attention at home and abroad, especially the new halopyridines containing iodine, bromine and chlorine play a very important role in the fields of medicine, pesticide and chemical industry, and become a synthetic pesticide and medicine. The direction of innovation for new drugs. The synthetic method of halopyridine generally includes polyhalogenated hydrocarbon ring method and pyridine halogenation method, but the former synthetic route is long, and yield is low, and impurity is many, and synthetic difficulty is big; The latter synthetic route is short, and impurity is few, synthetic difficulty is less, Has become the main synthetic method of halopyridine. [0003] 2-iodo-3-bromo-5-chloropyridine is an important intermediate in the synthesis of PLK (P...

Claims

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Application Information

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IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 赵春深柴慧芳周志旭乐意刘力滕明刚黄筑艳
Owner GUIZHOU UNIV
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